20 Lunches, 20 Insights

11 min read

I did it! I’ve coached 20 entrepreneurs in 7 cities in 4 months.

My mission was to give a boost to radically new, positive impact business during my 6 month sabbatical. In exchange for lunch I offered up my expertise, and met some talented and passionate people throughout the world. I coached and consulted freelancers, digital nomads, first time entrepreneurs and seasoned veterans, duos and teams of 100. We covered everything from leadership challenges and personal development to business development, branding, design and proposition development. It’s been an awesome ride.

Here’s what I learned:

Being an entrepreneur in S.E. Asia means eating with chopsticks

Several entrepreneurs spoke of the inescapable need to forge links with locals.

There is tons of opportunity, but you can’t forego local connections. Locals bridge the language gap, enable business/land ownership in some countries, facilitate hellish bureaucracy, and provide a network to employees and new business. It requires lots of trust too. Local business partners can walk away with your business or be there for the long haul. In some cultures it’s OK to ‘steal’ from the workplace, in others you won’t ever hear dissent or see proactive thinking. Yet the middle class is exploding and opportunities abound, so learn how to use your chopsticks.

Business doesn’t have to be a dirty word

Positive karma = positive business. While I don’t actually believe in karma, on the road people consistently applauded my model to exchange lunch for coaching/consulting.

The fact is that the best business is always a reciprocal virtuous circle. People react better to a story that is about meaningful mutual gain, rather than a story of exploitation or financial transaction. Business with positive impact starts from a mindset of building value for others, which makes others intrinsically motivated to be a part of your business. For e.g., look at the success of Tom’s shoes model of buy 1 give 1 to the needy, which all but eliminated the need for a marketing budget. Consider alternative forms of marketing and business models to build in positive impacts for an audience wider than yourself, and enjoy the positive boomerang effect it creates.

Design is a coaching tool

Each session I had was a challenge in aligning the values and goals of the entrepreneurs with their business. Design methods made this process easy and practical.

Design is about creating compelling futures in products and services, and making them tangible through prototypes and storytelling. But you can create future versions of yourself! Design your life. Explore your own intuition through alternatives and feeling your way through it with prototypes. Make these alternatives concrete to help get out of your head! Try on that new suit, heck try on a few until you feel like you should. I believe a good design facilitator has the tools that naturally apply to coaching, tools that uncover deeper meaning, help make your future-self tangible, and helps you creatively explore all your personal potential.

The passive-income energy trap

Passive doesn’t exist. Many freelancers and entrepreneurs felt the need to diversify with a ‘passive income’ stream through books, property investment, or e-courses. In each session we rediscovered that these businesses not only take time to create and maintain, but almost always require you to do things you don’t like.

If you are looking to diversify your income stream, be clear with yourself about what level of energy you are willing to invest. Seek ways to automate or delegate energy drains.

Design is a tool for creating business portfolios

A veteran entrepreneur needed to judge the viability, feasibility and desirability of a range of new business ideas in relation to his existing businesses. Using design techniques we walked through 3 ideas, considered alternative business models and propositions, analyzed customer needs and insights, and designed in synergies with his existing businesses. In 1.5 hours we determined the strongest idea and key assumptions to test.

Hopefully you know that design is fundamental to lean startup (think protoyping and customer empathy tools, more can be found here), but have considered how you can use design to build a portfolio of businesses? Serial entrepreneurs or conglomerates can leverage existing product lines or services by building businesses with inherent synergies. For e.g., Alphabet owns Uber and Waymo (self driving car BU) this is no accident!

A clear vision can alleviate the need to micro-manage

Entrepreneurs often confessed to being seduced by the need to control everything, which strangled growth. One entrepreneur described how she couldn’t scale because she was spending hours on content, and delegating meant trusting others to do a good job. Clearly defining the vision helped reprioritize her time and enabled her to step away from content to build the business.

Defining a vision enables sacrifice. It gives you permission to delegate, expedite or automate tasks that sacrifice some quality because the net reward is higher. Instead of doing it yourself, coach others to do what you are already good at – which lets you do what you want to become good at. More about how to roadmap your way to a vision in this post.

Scaling through traction and engagement, which starts with you

One entrepreneur needed programmers – which meant engaging those in his network to become committed to his cause. Another needed to prove traction to get funding, and another needed more consistent clients – both of which meant building out from friends to a second and then third degree network.

The world is getting busier and louder. It’s hard to be heard. Increasingly there is the need to create small communities that are loyal and build your business from the ground up. That means your personal network is key. For some this may mean big and loose, for others powerful and tight-knit.

Time management: big picture to small picture

What next? Where to start? Nearly all the entrepreneurs I spoke to grapple with maximizing their time. Each coaching session always went from big picture to small, giving perspective and priority – and more confident and relaxed entrepreneurs!

Some simple rules of thumb can help day to day prioritization, like using the 80/20 rule. When you know what 20% of actions really contribute to your goals then you can start with those, but every once and a while you need to recalibrate your big picture to make sure you are effective (check out this post on how to multiply your time). Zoom from big-picture targets to bite-size actions.

A ‘net positive mindset’ and avoiding burnout

One entrepreneur was on the edge of a burnout for 3 years. He knew himself well, he knew what he needed to solve yet was drowning in it nonetheless. So we built him a personal plan that remedied the source of his unhealthy stress in his role, daily activities, and mindset.

Panic seems to stem from being overwhelmed with things that give you no energy. Part of building a positive business for the world is building one that is positive for yourself. If you can bring balance to your life you can bring balance to systems greater than yourself. Build a business where you become a little bit healthier every day. You should strive to be net positive. If you find yourself down the road swamped by all the things you don’t thrive on, you must restructure the rules of engagement in your business until you can build-in what gives you energy – and eliminate, automate or delegate what doesn’t. Check out this blog post for more.

Confidence

Many entrepreneurs I met chose alternative education and career paths. The result is that sooner or later they question their skills in relation to industry standards or how to reposition themselves in a better (yet believable) way. What helped was defining a compelling vision of the self and defining a new story and action plan to transcend insecurities and start the self-prophesizing reality.

Nobody should let today’s insecurities hold themselves back. Design your dream, fake it till you make it and leverage what you are already good at to get momentum going. More in this post on how to learn anything.

Decision-making is an overlooked competence

Two co-founders found themselves constantly rethinking decisions. We built a decision-making checklist and process that aligned with their responsibilities and personal dynamic.

Startups don’t have the operational basis of a regular business with protocols for reporting and decision making. With a simple protocol in place you can make higher quality decisions, move forward with confidence, and distill learnings. You can more effectively use your time by planning work that leads up to your next decision moment (think Minimum Viable Product process)

Minimum Viable Products (MVP) are too often focused on a product

An industry veteran of 30 years was setting out to build a service, yet struggling to find the confidence to invest 500K of her own money to build the app. Rather than jumping to a semi-functional product we refocused her efforts into testing assumptions in a step-by-step process.

Building confidence to invest time or money into the next step of a business is a process of checking assumptions and building proof, not about defining what level of final product you need to test.

Envision future versions to pivot with agility

When assessing a business idea, entrepreneurs always benefited from thinking in future versions of the business. In one case the conclusion was creating a high cash-flow version first, which would then pay for enough employees to start the service-intensive versio

Envisioning the future versions builds strategy into your launch and makes it easier to pivot through MVP testing and after launch. More on how to do this in this blog post.

The 3 musketeers: Meaning, Impact & Authenticity

A reoccurring theme in the sessions was the desire for these three. These aspects seemed a given in any discussion I had. As an aside, while I think these motivations hold true for positive impact businesses, I don’t think they hold true for those seeking to make a quick buck.

Daniel Pink argued that motivation is determined mastery of a skill, autonomy in tasks, and aligning purpose with that of the company. This seems true of employees but not entrepreneurs. Entrepreneurs are more externally oriented. They desire to use their business to create meaning in society, are energized by seeing their impact, and make choices based on authentic alignment with their personal values. For employees urged to be more entrepreneurial in their work, designing meaning at work will become increasingly important (check out this post for how).

The power of coaching lies in giving yourself permission to be self-critical

Those who got the most out of our Working Lunches where those that gave themselves permission to be vulnerable and reflect critically about themselves.

Coaching injects new thinking into old behaviours, offering other external perspectives. As individuals we have difficulty truly being objective and self-critical – even coaches need coaching! Making this permission to be self-critical explicit as part of the coaching relationship helps frame the discussion and make it effective.

Leadership as a founder’s trap

Entrepreneurs are natural visionaries but are not necessarily leaders. I found many had a clear vision on the future but were daunted by persuading others to join their cause. Leadership challenges often emerged as a great limitation to their ability to scale and grow their business.

Entrepreneurs busy beavering away on their business may forget to do any personal development. Yet new business is about change, and leadership is about helping people grapple with change. Essential to growing your business is growing as a leader. Set targets to develop your personal style of leadership (and enjoy the benefits of ownership by investing in your primary employee).

Introverts may struggle to build a personal brand

Many founders and freelancers wanted to avoid the limelight, but struggled with how to build a brand and notoriety.

Not everyone has the charm of Tony Robbins, or the expertise. My thoughts are to find other ways to tell your story. Daft Punk are two faceless icons, Prince became ‘Symbol’. Make your introverted-ness a story in itself. Or make the brand focused on the unique format or USP, even if it is just you behind the work. The point is that people need strong associations to build the brand on – if it’s not your charm or expertise, then it needs to be something else that is just as compelling. There are options if you look for them, here’s a blog post about storytelling your way to a new brand positioning.

The new workplace is temporary

I visited a number of co-working spaces on my journey and heard mixed reviews from those that work there.

Co-working spaces have only begun to disrupt how we work. You start to see the advantages when you add to temporary workspaces concepts like flex hours and remote working for teams. Corporations will be drawn to them because they do not have all the expertise and creativity in-house. Future co-working spaces will focus on intense collaborations, focused on a particular product or competence. The power lies in bringing together fresh perspectives and passionate people in bespoke contexts that boost social interactivity and bonding. Workers are happier and the quality of work improves. Check out this post for more.

Expertise is not a substitute for boldness

People were surprised by the idea of Working Lunch, they said the story was clear and bold. This boldness made it easy to find people to coach. The story of Working Lunch was far more compelling than my CV.

Do you have what it takes to be an entrepreneur?

An entrepreneur takes action rather than writes long blog posts. Nah.. just kidding. But I don’t think there is a recipe, just be yourself and persevere. 20 Insights is 19 too many for an entrepreneur anyways…:)

P.s. If you know of a leader looking to build a business with a positive impact, and who could use a boost, I would love to see if I can help. Please forward my website http://ourworkinglunch.com/. Currently I’m in Vancouver, Canada.